Diastereoselective conjugate addition to chiral α,β-unsaturated carbonyl systems in aqueous media: An enantioselective entry to α- and γ-hydroxy acids and α-amino acids

Chemistry - A European Journal

Volumn 9, Issue 17, 2003, Pages 4179-4187

  Suárez, Rosa M ^a   Pérez Sestelo, José ^a   Sarandeses, Luis A ^a  

^a UNIVERSITY OF A CORUÑA   (Spain)

Author keywords

Aqueous media; Asymmetric synthesis; Diastereoselectivity; Michael addition; Radicals

Indexed keywords

HYDROXYLATION; OLEFINS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

CONJUGATE ADDITION;

AMINO ACIDS;

AMINO ACID; AMINO ACID DERIVATIVE; CARBONYL DERIVATIVE; COPPER; HYDROXYACID; HYDROXYL GROUP; IODIDE; KETONE DERIVATIVE; METHYLENEDIOXOLANONE; METHYLENEOXAZOLIDINONE; UNCLASSIFIED DRUG; ZINC;

ADDITION REACTION; AQUEOUS SOLUTION; ARTICLE; CHEMICAL REACTION; CHIRALITY; CONJUGATION; ENANTIOSELECTIVITY; GEOMETRY; HYDROLYSIS; ISOMER; STEREOCHEMISTRY;

AMINO ACIDS; COPPER; ESTERS; HYDROCARBONS, IODINATED; HYDROXY ACIDS; OXAZOLIDINONES; STEREOISOMERISM; WATER; ZINC;

EID: 3242727853     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200304790     Document Type: Article

References (71)

1. a) A. Lubineau, J. Auge in Modern Solvents in Organic Synthesis (Ed.: P. Knochel), Springer, Berlin, 1999, pp. 1-39;
2. b) P. A. Grieco, Organic Synthesis in Water, Blackie Academic & Professional, London, 1998;
3. c) C.-J. Li, T-H. Chan, Organic Reactions in Aqueous Media, Wiley, New York, 1997;
4. d) C.-J. Li, Chem. Rev. 1993, 93, 2023-2035.
5. U. M. Lindström, Chem. Rev. 2002, 102, 2751-2772.
6. a) P. Perlmutter, Conjugate Addition in Organic Synthesis, Pergamon, Oxford, 1992;
7. b) B. E. Rossiter, N. M. Swingle, Chem. Rev. 1992, 92, 771-806;
8. c) J. Leonard, E. Diez-Barra, S. Merino, Eur. J. Org. Chem. 1998, 2051-2061;
9. d) N. Krause, A. Hoffmann-Röder, Synthesis 2001, 171-196.
10. a) Z. G. Hajos, D. R. Parrish, J. Org. Chem. 1974, 39, 1612-1615;
11. b) U. Eder, G. Sauer, R. Wiechert, Angew. Chem. 1971, 83, 492-493; Angew. Chem. Int. Ed. Engl. 1971, 10, 496-497;
12. b) U. Eder, G. Sauer, R. Wiechert, Angew. Chem. 1971, 83, 492-493; Angew. Chem. Int. Ed. Engl. 1971, 10, 496-497;
13. c) N. Harada, T. Sugioka, H. Uda, T. Kuriki, Synthesis 1990, 53-56.
14. a) E. Keller, B. L. Feringa, Tetrahedron Lett. 1996, 37, 1879-1882;
15. b) E. Keller, B. L. Feringa, Synlett 1997, 842-844;
16. c) Y. Mori, K. Kakumoto, K. Manabe, S. Kobayashi, Tetrahedron Lett. 2000, 41, 3107-3111;
17. d) S. Venkatraman, Y. Meng, C-J. Li, Tetrahedron Lett. 2001, 42, 4459-4462;
18. e) S. Shimizu, S. Shirikawa, T. Suzuki, Y. Sasaki, Tetrahedron 2001, 57, 6169-6173;
19. f) D. Bensa, J.-M. Brunel, G. Buono, J. Rodriguez, Synlett 2001, 715-717.
20. a) T.-S. Huang, C.-J. Li, Org. Lett. 2001, 3, 2037-2039;
21. b) T.-S. Huang, C.-J. Li, Chem. Commun. 2001, 2348-2349;
22. c) H. Miyabe, M. Ueda, A. Nishimura, T. Naito, Org. Lett. 2002, 4, 131-134.
23. F. M. da Silva, J. Jones, Jr., J. Braz. Chem. Soc. 2001, 12, 135.
24. a) C. Petrier, C. Dupuy, J. L. Luche, Tetrahedron Lett. 1986, 27, 3149-3152;
25. b) J. L. Luche, C. Allavena, Tetrahedron Lett. 1988, 29, 5369-5372;
26. c) J. L. Luche, C. Allavena, C. Petrier, C. Dupuy, Tetrahedron Lett. 1988, 29, 5373-5374.
27. a) B. Giese, W. Damm, M. Roth, M. Zehnder, Synlett 1992, 441-443;
28. b) P. Erdmann, J. Schäfer, R. Springer, H.-G. Zeitz, B. Giese, Helv. Chim. Acta 1992, 75, 630-644;
29. c) M. Roth, W. Damm, B. Giese, Tetrahedron Lett. 1996, 37, 351-354.
30. a) P. Cintas, J.-L. Luche in Synthetic Organic Sonochemistry (Ed.: J.-L. Luche), Plenum, London, 1998, pp. 223-227. For more recent applications see: b) R. Lavilla, O. Coll, J. Bosch, M. Orozco, F. J. Luque, Eur. J. Org. Chem. 2001, 3719-3729; c) M. Okue, H. Kobayashi, K. Shin-ya, K. Furihata, Y. Hayakawa, H. Seto, H. Watanabe, T. Kitahara, Tetrahedron Lett. 2002, 43, 857-860.
31. a) P. Cintas, J.-L. Luche in Synthetic Organic Sonochemistry (Ed.: J.-L. Luche), Plenum, London, 1998, pp. 223-227. For more recent applications see: b) R. Lavilla, O. Coll, J. Bosch, M. Orozco, F. J. Luque, Eur. J. Org. Chem. 2001, 3719-3729; c) M. Okue, H. Kobayashi, K. Shin-ya, K. Furihata, Y. Hayakawa, H. Seto, H. Watanabe, T. Kitahara, Tetrahedron Lett. 2002, 43, 857-860.
32. a) P. Cintas, J.-L. Luche in Synthetic Organic Sonochemistry (Ed.: J.-L. Luche), Plenum, London, 1998, pp. 223-227. For more recent applications see: b) R. Lavilla, O. Coll, J. Bosch, M. Orozco, F. J. Luque, Eur. J. Org. Chem. 2001, 3719-3729; c) M. Okue, H. Kobayashi, K. Shin-ya, K. Furihata, Y. Hayakawa, H. Seto, H. Watanabe, T. Kitahara, Tetrahedron Lett. 2002, 43, 857-860.
33. a) L. Castedo, J. L. Mascareñas, A. Mouriño, L. A. Sarandeses, Tetrahedron Lett. 1988, 29, 1203-1206;
34. b) J. L. Mascareñas, L. A. Sarandeses, L. Castedo, A. Mouriño, Tetrahedron 1991, 47, 3485-3498;
35. c) J. L. Mascareñas, J. Pérez Sestelo, L. Castedo, A. Mouriño, Tetrahedron Lett. 1991, 32, 2813-2816;
36. d) J. Pérez Sestelo, J. L. Mascareñas, L. Castedo, A. Mouriño, J. Org. Chem. 1993, 58, 118-123;
37. e) J. Pérez Sestelo, J. L. Mascareñas, L. Castedo, A. Mouriño, Tetrahedron Lett. 1994, 35, 275-278.
38. J. Pérez Sestelo, I. Cornella, O. de Uña, A. Mouriño, L. A. Sarandeses, Chem. Eur. J. 2002, 8, 2747-2752.
39. J. Pérez Sestelo, O. de Uña, A. Mouriño, L. A. Sarandeses, Synlett 2002, 715-719.
40. R. M. Suárez, J. Pérez Sestelo, L. A. Sarandeses, Synlett 2002, 1435-1438.
41. For reviews on radical reactions, see: a) N. A. Porter, B. Giese, D. P. Curran, Acc. Chem. Res. 1991, 24, 163-171; b) N. A. Porter, B. Giese, D. P. Curran, Stereochemistry of Radical Reactions, VCH, Weinheim, 1996; c) M. P. Sibi, N. A. Porter, Acc. Chem. Res. 1999, 32, 163-171, d) M. P. Sibi, S. Manyem, Tetrahedron 2000, 56, 8033-8061; e) H. Yorimitsu, H. Shinokubo, K. Oshima, Synlett 2002, 674-686.
42. For reviews on radical reactions, see: a) N. A. Porter, B. Giese, D. P. Curran, Acc. Chem. Res. 1991, 24, 163-171; b) N. A. Porter, B. Giese, D. P. Curran, Stereochemistry of Radical Reactions, VCH, Weinheim, 1996; c) M. P. Sibi, N. A. Porter, Acc. Chem. Res. 1999, 32, 163-171, d) M. P. Sibi, S. Manyem, Tetrahedron 2000, 56, 8033-8061; e) H. Yorimitsu, H. Shinokubo, K. Oshima, Synlett 2002, 674-686.
43. For reviews on radical reactions, see: a) N. A. Porter, B. Giese, D. P. Curran, Acc. Chem. Res. 1991, 24, 163-171; b) N. A. Porter, B. Giese, D. P. Curran, Stereochemistry of Radical Reactions, VCH, Weinheim, 1996; c) M. P. Sibi, N. A. Porter, Acc. Chem. Res. 1999, 32, 163-171, d) M. P. Sibi, S. Manyem, Tetrahedron 2000, 56, 8033-8061; e) H. Yorimitsu, H. Shinokubo, K. Oshima, Synlett 2002, 674-686.
44. For reviews on radical reactions, see: a) N. A. Porter, B. Giese, D. P. Curran, Acc. Chem. Res. 1991, 24, 163-171; b) N. A. Porter, B. Giese, D. P. Curran, Stereochemistry of Radical Reactions, VCH, Weinheim, 1996; c) M. P. Sibi, N. A. Porter, Acc. Chem. Res. 1999, 32, 163-171, d) M. P. Sibi, S. Manyem, Tetrahedron 2000, 56, 8033-8061; e) H. Yorimitsu, H. Shinokubo, K. Oshima, Synlett 2002, 674-686.
45. For reviews on radical reactions, see: a) N. A. Porter, B. Giese, D. P. Curran, Acc. Chem. Res. 1991, 24, 163-171; b) N. A. Porter, B. Giese, D. P. Curran, Stereochemistry of Radical Reactions, VCH, Weinheim, 1996; c) M. P. Sibi, N. A. Porter, Acc. Chem. Res. 1999, 32, 163-171, d) M. P. Sibi, S. Manyem, Tetrahedron 2000, 56, 8033-8061; e) H. Yorimitsu, H. Shinokubo, K. Oshima, Synlett 2002, 674-686.
46. a) D. Seebach, R. Naef, G. Calderari, Tetrahedron 1984, 40, 1313-1324;
47. b) J. Zimmermann, D. Seebach, Helv. Chim. Acta 1987, 70, 1104-1114.
48. a) A. L. J. Beckwith, C. L. L. Chai, J. Chem. Soc. Chem. Commun. 1990, 1087-1088;
49. b) G. Kneer, J. Mattay, Tetrahedron Lett. 1992, 33, 8051-8054;
50. c) A. L. J. Beckwith, C. L. L. Chai, Tetrahedron 1993, 49, 7871-7882.
51. T. Itaya, A. Mizutani, Tetrahedron Lett. 1985, 26, 347-350.
52. a) M. J. Dunn, R. F. W. Jackson, J. Pietruzska, D. Turner, J. Org. Chem. 1995, 60, 2210-2215;
53. b) R. F. W. Jackson, K. James, M. J. Wythes, A. Wood, J. Chem. Soc. Chem. Commun. 1989, 644-655.
54. D. Seebach, A. Fadel, Helv. Chim. Acta 1985, 68, 1243-1250.
55. J. R. Axon, A. L. J. Beckwith, J. Chem. Soc. Chem. Commun. 1995, 549-550.
56. S. D. Bull, A. N. Chernega, S. G. Davies, W. O. Moss, R. M. Parkin Tetrahedron 1998, 54, 10379-10388.
57. S. Takano, A. Kurotaki, M. Takahashi, K. Ogasawara, Synthesis 1986, 403-406.
58. a) V. L. Patrocinio, P. R. R. Costa, C. R. D. Correia, Synthesis 1994, 474-476;
59. b) J. S. Costa, A. G. Dias, A. L. Anholeto, M. D. Monteiro, V. L. Patrocinio, P. R. R. Costa, J. Org. Chem. 1997, 62, 4002-4006;
60. c) T. Moriwaka, Y. Washio, S. Harada, R. Hanai, T. Kayashita, H. Nemoto, M. Shiro, T. Taguchi, J. Chem. Soc. Perkin Trans. 1 1995, 271-281;
61. d) K. Nilsson, C. Ullenius, Tetrahedron 1994, 50, 13173-13180;
62. e) M. Nomura, S. Kanemasa, Tetrahedron Lett. 1994, 35, 143-146;
63. f) J. Leonard, G. Ryan, P. A. Swain, Synlett 1990, 613-614.
64. a) R. W. Hoffmann, Chem. Rev. 1989, 89, 1841-1860;
65. b) W. Smadja, M. Zahouily, M. Malacria, Tetrahedron Lett. 1992, 33, 5511-5514;
66. c) T. Morikawa, Y. Washio, M. Shiro, T. Taguchi, Chem. Lett. 1993, 249-250;
67. d) A. Mengel, O. Reiser, Chem. Rev. 1999, 99, 1191-1223.
68. J. Leonard, S. Mohialdin, D. Reed, G. Ryan, P. A. Swain, Tetrahedron 1995, 51, 12843-12858.
69. A. Krief, L. Provins, A. Froidbise, Tetrahedron Lett. 1998, 39, 1437-1440.
70. G. B. Kauffman, L. A. Teter, Inorg. Synth. 1963, 7, 9-12
71. W. C. Still, M. Kahn, A. Mitra, J. Org. Chem. 1978, 43, 2923-2925.